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What if Jon Lester’s Red Sox Career Continued?

The Prologue

In 2014, Boston was at a crossroads with their franchise pitcher. Jon Lester’s Red Sox Career was in question due to his then upcoming free agency. He had claimed to be willing to take a “hometown discount” so he could stay in Boston. But when Red Sox brass reportedly offered him a 4-year/$70-million-dollar contract, the two sides never reached an agreement.

Lester stayed with the Sox for the beginning of the 2014 season and made the All-Star Game. However, the team was seemingly out of it at the trade deadline, and Lester was shipped to Oakland as a rental with Jonny Gomes in exchange for Yoenis Cespedes.

At the end of the season, Cespedes was traded to Detroit for Rick Porcello. Meanwhile, Lester still became a free agent. The Red Sox were in talks to re-sign him but faced huge competition from the Chicago Cubs. Thus, Jon Lester’s Red Sox career was in jeopardy.

Eventually, the Cubs won the bidding and signed Lester to a six-year, $155 million deal with a vesting option for a seventh year at $15 million. The move reunited him with both David Ross and Theo Epstein. John Lackey, who was also traded in July 2014, would join the club the following year.

What if Jon Lester’s Red Sox Career Continued??

But what if John Henry and Co. had signed Lester to a big deal of their own? Let’s say at around the same price the Cubs paid, or more.

Well for starters, David Price would either be a Yankee, a Cub, or a Cardinal.

Rick Porcello may or may not be on the roster. Depends on how comfortable they would’ve been with Lester, Clay Buchholz, and prospects like Rubby de la Rosa, Brandon Workman, and Anthony Ranaudo.

Only one of those guys (Workman) remains on the 40-man roster today. Eduardo Rodriguez, though still very young then, could have been another compliment.

Both Justin Masterson and Wade Miley wouldn’t have been acquired. Obviously, they were only placeholders until Price came along. But, of course, with Lester who needs Price?

Additionally, David Ross would’ve stayed with Boston for the remainder of his career. He and David Ortiz would’ve retired at the same time.

Dave Dombrowski wouldn’t have been hired because the Ben Cherington would’ve had less pressure to succeed if he had kept Epstein’s guys, like Lester, around to help. Likewise, I believe the Sox would’ve won more games in 2015 with one ace as opposed to five #4 starters.

So would the Cubs win the World Series in 2016 without Lester? Nope.

Instead, I bet Theo would’ve chased Price or Zack Greinke in the 2015 offseason. Especially if Lester had slipped away and the team failed to reach the NLCS. The ’16 Cubs would then, of course, have a similar campaign and reach the postseason. Only to lose Game 5 of the NLDS to the Giants with David Price on the mound.

The Giants would’ve made the World Series and played the young and exciting Red Sox (of course). Jon Lester would pitch Game 7 against Madison Bumgarner in an epic duel. Almost as good as the Cubs-Indians duel.

It’s a shame that the team who drafted, developed, and gave him everything didn’t resign him. Jon Lester is a hero to many – and his resilience through cancer, dominance on the mound, and consistent sportsmanship is legendary.